Phosphate → HCID 72707041, compound

HRID 595268Notes

Reaction equation

HRID 595268 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=2)[N:12]=[C:11]([C:26]2[CH:27]=[N:28][N:29]([CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[CH:30]=2)[CH:10]=1.P([O-])([O-])([O-])=O>C(Cl)Cl>[CH3:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[CH:18][N:17]=2)[N:12]=[C:11]([C:26]2[CH:27]=[N:28][N:29]([CH2:31][C:32]([OH:34])=[O:33])[CH:30]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 6422Trifluoroacetic acidHCID 131734582HCID 131734582, compound

Product 1

HCID 72707041HCID 72707041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

TFA (1.17 ml, 15.2 mmol) was added to a stirred solution of tert-butyl [4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1H-pyrazol-1-yl]acetate (330 mg, 0.76 mmol) in DCM (3.8 ml) at room temperature. The reaction mixture was stirred at 40° C. overnight. Upon cooling, the reaction mixture was poured into phosphate buffer pH 4 and extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in Et2O to afford [4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1H-pyrazol-1-yl]acetic acid as a pale yellow solid. [M+H]+ 378. found, 378

Workup

  1. temperatureUpon cooling
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-5bc82aed12d34dc79c56881f3f96b073
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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